Lamellar liquid crystals in viscuous oil product

ABSTRACT

Disclosed is a viscous oil product made by combining an oil or oil-containing product with a crystallizing agent, moderately heating the mixture and allowing the mixture to cool, forming lamellar liquid crystals. A crystal stabilizing agent is also disclosed. A uniquely healthy and palatable manner of providing essential fatty acids for consumption is disclosed.

FIELD OF THE INVENTION

[0001] The present invention is directed to the field of oils and moreparticularly to a general method of rendering oil-containing productsviscous by producing lamellar liquid crystals in the oil. In particular,it concerns a viscous oil product containing oil, a crystallizing agentand optionally a crystal-stabilizing agent or an essential fatty acid.

BACKGROUND OF THE INVENTION

[0002] Fats and oils are an important source of energy, have animportant role as carriers of fat-soluble vitamins and haveindispensable functional properties in improving the quality of foodproducts with respect to such properties as texture, flavor andstructure.

[0003] The therapeutic properties of some oils, such as olive oil andfish oil have been widely documented. Olive oil has been indicated ashaving a therapeutic effect in stomach ailments (1, 1a), increasingmemory (2), decreasing mortality from heart disease due to increasingblood flow (3) and softening skin (4). Additionally, olive oil is usedin relieving ear infection, may reduce the risk of certain cancers (5,6), decreases calcium loss from bones and increases mineral absorption(7). In children, olive oil and fish oil has been linked to stimulatinggrowth and development (8). Other oils recognized as being “healthy”include avocado oil, walnut oil and macadamia oil.

[0004] Food spreads such as margarine and butter are a preferred mannerof consuming oil products in the Western world. Food spreads are used inthe home and in industry for cooking, baking, and in the preparation ofsandwiches and numerous other food products. In recent years, attentionhas been directed to producing healthier food spreads in the form ofreduced fat alternatives to the existing products.

[0005] Margarines are generally water/oil emulsions. The taste ofmargarine and related food spreads is due mostly to water-solubleflavors, oil-soluble flavors and salt. Margarine type products containat least 80% of fat by weight. The fat content is made up mainly ofhydrogenated and partially hydrogenated fats and oils. As is known toone skilled in the art hydrogenated and partially hydrogenated fats andoils (suspected carcinogens) as well as trans isomer fatty acids(suspected as contributing to athersclerosis formation) are notconsidered particularly healthy for human consumption.

[0006] U.S. Pat. No. 4,226,895, U.S. Pat. No. 4,284,655 and U.S. Pat.No. 5,409,727 teach of food spreads that are all substantially an oil inwater emulsions. U.S. Pat. No. 5,360,626 teaches a food spreadcontaining an aqueous phase and an oil phase.

[0007] U.S. Pat. No. 5,360,626 discloses an edible food productcontaining an oil or fat thickened with a hardening agent comprising analkyl-substituted, non-nitrogen containing oil-soluble polymer having amolecular weight of at least 2000 Dalton.

[0008] U.S. Pat. No. 5,376,398 teaches a fat substitute useful forpreparing a reduced calorie food product, the fat substitute comprisingan edible triglyceride and a polytetramethylene ether glycol esterifiedwith a fatty acid entity. Additionally, U.S. Pat. No. 5,376,398 teachesa food product where the fat component thereof is a polyteramethyleneether glycol esterified with a fatty acid entity.

[0009] U.S. Pat. No. 6,117,476 and U.S. Pat. No. 6,156,369 teach edibleoil-based food spreads that overcome the problems discussed above. InU.S. Pat. No. 6,117,476 a waterless mixture composed of 90% to 98% oiland 2% to 10% monoglyceride gives a smearable product at normal eatingtemperature. In U.S. Pat. No. 6,156,369 a waterless mixture composed of85% to 98% oil, 2% to 15% monoglyceride and in some cases up to 0.05%emulsifier such as Tween® is disclosed. In both U.S. Pat. No. 6,117,476and U.S. Pat. No. 6,156,369 different edible oils are used but olive oiland fish oil are preferred. In both U.S. Pat. No. 6,117,476 and U.S.Pat. No. 6,156,369 any monoglyceride is used, but oleic or palmitic acidderivatives are preferred. In both case a process of manufacture isdisclosed where an oil/monoglyceride mixture is heated to no more than75° C.

[0010] It would be highly advantageous to have a viscous to solid oilproduct with a pleasing texture that can be made with no harmfuladditives and can be produced without heating to a degree which maycause the oil to become unhealthy.

[0011] Herein, the term “fat” and the term “oil” shall be usedinterchangeably to refer collectively to fats and oils.

REFERENCES

[0012] 1. Taits, N. S. “Use of olive oil in the treatment of ulcerpatients” in Urach. Delo. 1966, 7, 67.

[0013] 1a. Ricci, G. “L'olio di oliva in gastroenterologia” in 1stInternational Congress on the biological value of olive oil, Lacca(Italy) 10-12 October 1969, p.128.

[0014] 2. Harman, D. “Free radical theory of Aging: Effect of fat onlipid composition and function of the brain” in 3rd InternationalCongress On the biological value of olive oil. Canin, Creta. 1980, p.190.

[0015] 3. Berry M. E. et al. “Effects of diets rich in monounsaturatedfatty acids on plasma lipoproteins—The Jerusalem Study. IIMonounsaturated fatty acids vs. Carbohydrates” Am. J. Clin. Nat. 1992,56, pp.394-403.

[0016] 4. Pinckney, E. R.; et al. “The potential toxicity of excessivepolyunsaturates. Do not let the patient harm himself” Am. Heart J.,1973, 85, p.723.

[0017] 5. Trichopoula, A. et al. “Consumption of olive oil and specificfood groups in relation to breast cancer risk” Greece. J. of theNational Cancer Institute, 1995, 87(2).

[0018] 6. Bitterman. W. A. et al. “Environmental and nutritional factorssignificantly associated with cancer of the urinary tract amongdifferent ethnic groups” Urologic. Clinics of North America 1991, 18(3).

[0019] 7. Laval-Jeanet, A. M. et al. “Effets des lipides oleiques sur lacroissance et la composition de l'os en nutrition experimentale” in the3rd International Congress on the biological value of olive oil. Conea,Crete, 1980, p.309.

[0020] 8. Crawford, M. A. “The role of essential fats in human maternaland infant nutrition with special reference to brain growth” in the 2ndInternational Congress on the biology value of olive oil. Toremolinos1975, p.35.

SUMMARY OF THE INVENTION

[0021] The present invention is of a viscous oil product made of oil anda crystallizing agent, together forming lamellar liquid crystals and amethod to make the same. By viscous oil product is meant, for example,thickened liquid oils, homogenized oil-containing pastes as well assolid to semi-solid oil spreads (i.e. margarine-like products).According to a feature of the present invention the ratio of oil tocrystallizing agent is dependent on the desired degree of productsolidity desired. The ratio of oil to crystallizing agent is preferablyfrom about 9 to 1 to about 49 to 1 and more preferably from about 12 to1 to about 24 to 1.

[0022] According to a feature of the present invention by “oil” is meanta liquid oil or fat (e.g. oils from olives, avocado, rapeseed, soybean,sunflower, peanut, safflower, cottonseed, coconut, rice bran,mustardseed, camelina, chia, fish, flaxseed, perilla, palm, sesame,peanut, almond, pine nut, macadamia, borage, primrose and corn as wellas mixtures of different fats and oils and mixtures of palm oil withpalm stearin or palm kernel stearin). According to a further feature ofthe present invention the term “oil” also includes oily products,especially oily plant products having at least about 15% oil by weight,more preferably above about 20%, even more preferably above about 30%and most preferably above about 40%. By oily plant products is meantpastes such as tahini (sesame paste) and oil containing plant-parts suchas sesame seeds, peanuts, almonds, walnuts, pine nuts and macadamianuts. Also included are mixtures of different oils and oily products.

[0023] According to a feature of the present invention suitablecrystallizing agents include monoglycerides, as described in U.S. Pat.No. 6,117,476 and U.S. Pat. No. 6,156,369. Additional crystallizingagents, divided into eight families, include:

[0024] a) phospholipids, especially lechitins. Lechitins are especiallypreferred as the phosphatidyl serine or phosphatidyl choline forms oflechitin are considered to be important for brain functioning;

[0025] b) glycerol esters of fatty acids. Amongst this family ofcrystallizing agents are two categories: 1) monoacylglycerol esters(glycerol mono fatty acids, monoglyceride esters) and 2) diacylglycerolesters of fatty acids (glycerol di fatty acid esters, di glycerideesters). Also included amongst the second family of crystallizing agentsare mixtures of categories 1 and 2, the mixtures known asmonodiglycerides. The fatty acid part of a member of this family ofcrystallizing agents come from different sources, e.g. palm, soybeans,rapeseed, sunflower fish and tallow. Included are saturated andunsaturated fatty acids such as stearic, palmitic, lauric, oleic,linoleic, linolenic, behenic and archidic fatty acids;

[0026] c) polyglycerol esters of fatty acids. The polyglycerol estershave from one to ten fatty acids attached to a polyglycerol backbone.Included, for example, are decaglycerol decastearate (10.G.10.S.),diglycerol monostearate (2.G.1.S.), diglycerol monopalmitate (2.G.1.P.),triglycerol monostearate (3.G.1.S.), triglycerol monopalmitate(3.G.1.P.), hexaglycerol monostearate (6.G.1.S.), hexaglyceroltristearate (6.G.3.S.), decaglycerol octostearate (10.G.8.S.) anddecaglycerol octopalmitate (10.G.8P.);

[0027] d) propylene glycolesters (propylene glycol monofatty acidesters, propylene glycol difatty acid esters) including propylene glycolmono stearate (PGMS) and propylene glycol stearate (DPGMS);

[0028] e) sugar esters of fatty acids, especially saturated fatty acids,including complex mixtures of sucrose mono and di fatty acid esters ofvarious fatty acid chain length including, for example, sucrose monostearate, sucrose monopalmitate, sucrose monolaurate and sucrosemonooleate;

[0029] f) sodium or potassium stearoyl lactylates;

[0030] g) polyglycerol poly ricinoleate (PGPR).

[0031] According to a feature of the present invention included areindividual crystallizing agents as well as mixtures of crystallizingagents, including mixtures of crystallizing agents taken from one ormore families.

[0032] As is discussed hereinbelow, the crystallizing agents are usedfor the production of lamellar liquid crystals in oil, consequentlyincreasing the viscosity of the oil. Said otherwise, the method of thepresent invention includes the making of a viscous oil-containingproduct by dissolving a crystallizing agent in an oil-containingsubstrate and thus forming lamellar liquid crystals in theoil-containing substrate.

[0033] The present invention is also of a viscous oil product containinga mixture of oil, a crystallizing agent and a crystal stabilizing agenttogether forming lamellar liquid crystals and a method to make the same.According to a feature of the present invention, when used the weight ofcrystal stabilizing agent added is preferably from about 0.001% to about5% and more preferably from about 0.1% to about 2% of the weight of theoil in the product. According to a feature of the present invention thecrystal stabilizing agent added is a powdered fat fraction with amelting point less than about 80° C. such as Akofine PO5®, Akofine R® orCessa Powder 60®. Details of crystal stabilizing agents according to thepresent invention are described in “Food and Marketing Technology” April2002 pp. 44-45, which is incorporated by reference for all purposes asif fully set forth herein. Other suitable crystal stabilizing agentsinclude Akofine K25®, Akofine SP01®, Akofine D08® and Akofine WOO®.

[0034] According to a further feature of the present invention,oil/fat-soluble flavorings or oil/fat-soluble vitamins are added asadditional components of a viscous oil product of the present invention.

[0035] According to a further feature of the present invention, one ormore essential fatty acids (EFAs) are added as a component of theviscous oil product of the present invention. Preferred EFAs include DHA(docosahexaenoic acid) and EPA (eicosapentaenoic acid) from any source,most preferably as components of fish oil; ALA (alpha linolenic acid)from any source, preferably of non-animal origin, most preferably as acomponent of flax, camelina or safflower oil; GLA (gamma linolenic acid)from any source, most preferably as a component of borage seed orprimrose oil; CLA (conjugated linolenic acid), pure or as mixtures,especially 8-cis, 10-trans linolenic acid from any source.

[0036] The preparation of the viscous oil product of the presentinvention involves three main steps: combining the oil and crystallizingagent to make a mixture, heating and mixing the mixture untilhomogenous, and then cooling the mixture to form the viscous oil productof the present invention.

[0037] At room temperature crystallizing agents are generally notsoluble in oils. According to a feature of the present invention, thecrystallizing agents are preferably dissolved in the oil at temperaturesof from preferably 45° C. to about 120° C., more preferably from about45° C. to about 90° C., and even more preferably from about 45° C. toabout 75° C. At these temperatures, the crystallizing agents dissolveand the mixture is substantially transparent.

[0038] According to a feature of the present invention, during thecooling process properties of the product are improved by reducing thesize of the lamellar liquid crystals. A preferred way to reduce the sizeof the crystals is through homogenization of the mixture. Homogenizationcan be performed using the methods known in the art, for example,high-shear homogenization or piston homogenization.

[0039] According to a feature of the present invention, a crystalstabilizing agent is added. The temperature of the mixture must be highenough so that complete dissolution of the crystal stabilizing agent isachieved. Clearly, a mixture containing crystal stabilizing agent canalso be homogenized in order to reduce crystal size.

[0040] According to a feature of the present invention, when oxygensensitive substances are added to a product of the present invention(for example EFAs), the production process is performed in an inertatmosphere, specifically by de aerating the oil or the mixture at anyappropriate moment during the process (for example, by bubbling an inertgas such as nitrogen through the mixture) and maintaining the product inan inert atmosphere until the product solidifies.

[0041] According to the teachings of the present invention, when aproduct is made based on the use of an oily product, such as an oilyproduct of plant origin, the oily product is supplied in any convenientform such as a paste or solid. By solid is included the whole plant partsuch as whole nuts, grains and seeds (after having been properlyprepared, i.e. cleaned, shelled and the such) or fragments thereof suchas powders, flours, dusts, bits and chunks. During the productionprocess, mixing of the crystallization agent with the oily product alsoinvolves making any solid parts smaller (by, for example, bruising,comminuting, crushing, grinding, mashing, milling or macerating) to thepoint that the mixture has a paste-like consistency.

[0042] When using oily products, it may be necessary to performpasteurization. Such pasteurization can be advantageously performed aspart of the heating necessary for making the viscous oil-containingproduct of the present invention.

BRIEF DESCRIPTION OF THE FIGURES

[0043] The invention is herein described, by way of example only, withreference to the accompanying figures, wherein:

[0044]FIG. 1A is a reproduction of an image of a viscous oil product ofthe present invention at 25° C. using digital light microscopy (DLM)with differential interference (DI) taken using Nomarski Optics;

[0045]FIG. 1B is a reproduction of an image of a viscous oil product ofthe present invention at 25° C. using digital light microscopy (DLM)with differential interference (DI) and a crossed polar image;

[0046]FIG. 2 is a result of differential scanning calorimetrymeasurement of a viscous oil product of the present invention indicatingboth liquid and solid properties;

[0047]FIG. 3A is a reproduction of cryogenic temperature transmissionelectron microscope (cryo-TEM) image of a viscous oil product of thepresent invention composed of 0.5% stearic monoglyceride in olive oil;

[0048]FIG. 3B is a reproduction of cryogenic temperature transmissionelectron microscope (cryo-TEM) image of a viscous oil product of thepresent invention composed of 7% stearic monoglyceride in olive oil; and

[0049]FIG. 4 is the result of a small-angle X-ray scattering (SAXS)measurement of a viscous oil product of the present invention.

DETAILED DESCRIPTION OF THE INVENTION

[0050] The present invention is of a viscous oil product and a method ofmaking the same using only moderate heating thus reducing the productionof unhealthy oil-related byproducts. The product and the method of thepresent invention may be better understood with reference to theaccompanying description and figures. The viscous oil product containsno unhealthy additives and is virtually water-free, ensuring a longshelf life. The nearest prior art, U.S. Pat. No. 6,117,476 and U.S. Pat.No. 6,156,369 by the same inventor, teaches the use of monoglycerides tothicken oils and produce spreadable food products. The inventor hasfound that, unexpectedly and unpredictably, other compounds, not justmonglycerides, also achieve the thickening of oils by forming lamellarliquid crystals. Thus the present invention teaches of a productincluding an oil and a crystallizing agent.

[0051] Crystallizing agents useful according to the present inventioninclude monoglycerides, as described in U.S. Pat. No. 6,117,476 and U.S.Pat. No. 6,156,369 as well as additional crystallizing agents, dividedinto eight families, see hereinabove.

[0052] A first method of making a viscous oil product of the presentinvention involves mixing an oil, a crystallizing agent and additives toan elevated temperature, for example between about 45° C. and about 120°C., preferably between about 45° C. to about 90° C. and even morepreferably between about 45° C. to about 75° C. It is clear to oneskilled in the art that the order of heating and adding the oil, thecrystallizing agent and additives is a technical detail and not salientto the present invention. Subsequent to heating and after confirmationthat the mixture is homogenous, the mixture is allowed to cool leadingto formation of lamellar liquid crystals, preferably in the finalpackaging.

[0053] In general when a low proportion of crystallizing agent is used(up to about 3% by weight of the oil, and depending on the oil andcrystallizing agent) then, at room temperature, the viscous oil productof the invention is liquid but more viscous than the oil itself. Whenhigher proportions of crystallizing agent are used the product is solidbut smearable, like margarine, butter or paraffin wax.

[0054] The increased viscosity of oil treated according to the method ofthe present invention is a result of the unexpected and never beforeobserved formation of a lamellar liquid crystal structure in oil, seeExample 1. Thus, it must be made clear that practice of the presentinvention results in the hardening of oils and fats throughcrystallization to form lamellar liquid crystals. Such factors ascrystal morphology, crystal size, habit, population by volume andpopulation by number all influence the exact properties of the viscousoil product of the present invention.

[0055] It has been found that homogenization (for example by methodssuch as high-shear homogenization or piston homogenization) of a mixtureof the present invention during cooling allows formation of crystalsmuch smaller than those formed without such a homogenization step. Allthings being equal, the smaller the crystals in a viscous oil product ofthe present invention, the more esthetic and smearable the product is.Thus, a feature of the present invention is the addition of ahomogenization step. After heating and mixing, the temperature of themixture is allowed to cool during a homogenization step. Homogenizationpreferably occurs during the crystallization itself.

[0056] It has been found that the addition of a crystal-stabilizingagent to the mixture stabilizes the crystal structure of the finalproduct. While not wishing to be held to any one theory, it is believedthat the crystal-stabilizing agent wraps around the ends of the liquidcrystal lamellae, preventing smaller crystals from joining to producelarger crystals. Thus, a further feature of the present invention is theaddition of a crystal stabilizing agent, preferably powdered fat with amelting point less than about 80° C. Suitable crystal stabilizing agentsinclude Akofine PO5®, Akofine R® and Cessa Powder 60® marketed byKarlshamns (Karlshamn, Sweden). The amount of crystal stabilizing agentis preferably between about 0.001% and about 5% of the weight of theoil, and more preferably between about 0.1% and about 2% of the weightof the oil.

[0057] When used, a crystal stabilizing agent is added to the mixtureprior to crystal formation. When the temperature of the mixture ishigher than the melting point of the crystal stabilizing agent, a clearoil/crystallizing agent/crystal stabilizing agent phase results. Themixture is allowed to cool to a temperature when crystallization beginsso that the base oil/crystallizing agent/crystal stabilizing agent phasebecomes cloudy. The mixture is then allowed to cool farther to produce aproduct of the present invention. When the mixture is homogenized asdescribed hereinabove, homogenization is optimally performed duringcrystallization.

[0058] To a viscous oil product of the present invention, it is possibleto add additional oil soluble products, specifically essential fattyacids (vide infra), vitamins or flavorings such as lemon oil or garlicoil.

[0059] Homogenous Oily Pastes

[0060] A popular oil product known in the art is an oily paste. Crushinga naturally occurring seed or other plant part and then heating theresulting flour makes the paste. In such a fashion, products such assesame paste (tahini) are made. The tahini is then consumed as is orused as a component of a variety of edible products.

[0061] The problem with oily pastes such as tahini is that these aresubstantially non-homogenous products having an oil phase and a fiberphase made of relatively large fiber particles, proteins, carbohydratesand other oil-insoluble materials.

[0062] Prior art oily pastes can be made to be temporarily homogenous byvigorous mixing for use. Left to stand, for example during transport andstorage, the phases separate. After long-term storage, the phases mayirreversibly separate and the product consequently discarded.

[0063] In some cases, a paste cannot be made directly by crushing anoil-containing plant part. For example, when peanuts are ground, a pasteis not formed but rather there is separation into peanut oil and a hardpulp cake. To make the popular edible product known as peanut butter itis necessary to add significant amounts of unhealthy partiallyhydrogenated fats to make a homogenous spread.

[0064] The production of stable oily pastes without the addition ofunhealthy fats or oils is achieved by the method of the presentinvention. Although not wishing to be held to any one theory, it isbelieved that pulp and other oil-insoluble components are suspendedwithin the lamellae of the liquid crystal structure of the presentinvention. Thus, a paste of the present invention is homogenous, evenafter extended storage. Depending on the ratio of oil to crystallizingagent a paste of the present invention may be a homogenous liquid, aviscous paste (like prior art peanut butter) or a solid margarine-likeproduct.

[0065] According to a first embodiment of the homogenous oily paste ofthe present invention, to an oily paste (e.g., tahini) is added acrystallizing agent of the present invention. The mixture is heated,mixed and allowed to cool. A homogenization step to reduce crystal size,as described above, may be performed. A crystal stabilizing agent may beadded as described above. It is clear that to ensure that the homogenousoily paste of the present invention is homogenous, sufficient mixingmust be performed during the cooling process, ensuring that pulpparticles are effectively trapped inside the crystal structure of thefinal product.

[0066] In a second embodiment of the homogenous oily paste of thepresent invention, to an oily product, especially an oily plant product(e.g. crushed roasted peanuts) is added a crystallizing agent of thepresent invention. The mixture is then ground to a paste at an elevatedtemperature, as described hereinabove. Once a homogenous paste isformed, the mixture is allowed to cool. A homogenization step to reducecrystal size, as described above, may be performed. A crystalstabilizing agent may be added as described above. It is clear that toensure that the homogenous oily paste of the present invention ishomogenous, sufficient mixing must be performed during the coolingprocess, ensuring that pulp particles are effectively trapped inside thecrystal structure of the final product.

[0067] The preferred oily products for use in making the homogenous oilypaste of the present invention include tahini and sesame seeds (40%-60%oil by weight), peanuts (45%-55% oil by weight), almonds (45%-55% oil byweight), walnuts (50%-70% oil by weight), pine nuts (55%-65%) andmacadamia nuts (70-85% oil by weight). Exceptionally preferred arewalnuts which contain omega-3 fatty acids and macadamia nuts containingpalmitoleic acid and having a low omega-6 fatty acid content.

[0068] The amount of crystallizing agent added when making a homogenousoily paste of the present invention is as described hereinabove. Theexact amount of crystallizing agent added is dependent on the desiredviscosity of the homogenous oily paste, the nature of the crystallizingagent and the nature of the oily product. As with other oil products ofthe present invention. the amount of crystallizing agent in a large partdetermines the exact properties of the product. Lower proportions ofcrystallizing agents leave homogenous oily paste of the presentinvention in the form of a homogenous but viscous liquid appropriate forpouring, for example as a sauce or for cooking. Higher proportions ofcrystallizing agent produce a solid but smearable homogenous oily pasteof the present invention, much like margarine.

[0069] To the homogenous oily paste of the present invention it ispossible to add additional oil soluble products, specifically essentialfatty acids (vide infra), vitamins or flavorings such as lemon oil orgarlic oil.

[0070] EFA Containing Oil Products

[0071] A number of fatty acids, termed essential fatty acids (EFAs) arebeneficial for human health when consumed.

[0072] Two exceptionally beneficial EFAs are docosahexaenoic acid (DHA)and eicosapentaenoic acid (EPA). DHA and EPA are found in the oil ofcertain cold water fish (e.g. anchovy, herring, mackerel, menhaden,sardine, and salmon) and can theoretically be consumed directly.However, fish oil is generally considered as having an offensive flavorand smell. Fish flesh can be consumed as a source of DHA and EPA, but isgenerally difficult to use as a general source of nutrient. Fish isnotoriously difficult to transport and store, many fish species areendangered and may become expensive, and not everyone likes to eat sushior Hollandse Nieuw. Cooking fish before consumption damages EFAstherein.

[0073] Another essential fatty acid considered beneficial is alphalinolenic acid (ALA) found in not normally eaten crops such as flax,camelina and safflower. ALA is healthy and is also a precursor to DHAand EPA. Therefore it is an ideal product for people who chose not toconsume animal-based (including fish-based) products for variousreasons. It is advisable for such people to eat extra amounts of ALA andderivatives as alternatives to the consumption of DHA/EPA. There are fewtasty products that supply ALA.

[0074] Another essential fatty acid considered beneficial is gammalinolenic acid acid (GLA) found in not normally eaten crops such asborage seed or in primrose oil or linolenic acid (LA) which is convertedinto gamma-linolenic acid (GLA) in the body. There exists evidence thatconsumption of conjugated linolenic acids (CLA) especially doubleunsaturated conjugated linolenic acids, and most preferably 8-cis,10-trans linolenic acid can help prevent or even cure cancer.

[0075] Clearly there is interest in promoting the consumption of theabove-mentioned and other EFAs. Obviously it is preferable that EFAs andderivative be consumed as “normal foods” and not as dietary supplementsor other forms that require a change in consumer behavior. To gainacceptance, such a normal food“must be tasty, easy to use, normallyeaten and not require a change in lifestyle. However, this is madedifficult by the fact that EFAs decompose at elevated temperatures andare susceptible to decomposition in the presence of both water and air.To maintain the beneficial properties of EFAs it is necessary to preventcontact with water and oxygen. Further, fatty acids must not be heatedto a temperature where decomposition and concomitant loss in beneficialproperties occurs.

[0076] Liquid oils are an unsuitable medium for the delivery of EFAs.Liquid oil is not routinely imbibed, and is often used for cooking,especially frying. Routine decanting of oil from a bottle exposes theoil to air. In the most favorable use, where liquid oil is used as asalad oil, much oil does not adhere to the salad component and the oilis wasted. It is also important to note that most salad oils are refinedat elevated temperatures, rendering them relatively unhealthy.

[0077] In any case, many people in the world prefer to use hardened orsolidified fats as opposed to oil when cooking baking or frying. Thiscan be a result of culture, texture, tradition or simply the ease ofmeasuring a required amount. Thus despite the fact that liquid oil maybe healthier for frying (olive oil, for example, is consideredrelatively healthy for frying), many people continue to use less healthysolid fats or solidified oils.

[0078] In the Western world fat is preferably consumed in the form of aspread on a carbohydrate substrate such as potatoes, bread or crackers.

[0079] Typically lard, fowl fats or butter contain between 15% and 20%water that beyond causing EFA decomposition also leads to rancidity,shortening product shelf-life. Further, the higher-animal origin oflard, fowl fats or butter is suspected as being unhealthy.

[0080] Margarine and margarine-like products are also an unsuitablemedium for the delivery of EFAs. Margarine and margarine type productstypically contain hydrogenated and partially hydrogenated oils(suspected carcinogens) as well as trans isomer fatty acids (suspectedas contributing to athersclerosis formation). The use of healthy oils(such as olive oil) in margarine-type products is not a successfulstrategy. The necessity for emulsifier (often higher than 35%) dilutesthe health benefits which may be gained from the use of a healthy oil.The margarine manufacture process (including heating and partialhydrogenation) inherently reduces the healthiness of a margarineproduct. Margarines typically include roughly 35% water that beyondcausing EFA decomposition also leads to rancidity. shortening productshelf-life.

[0081] Thus, it is desirable to produce a solid EFA-containing foodproduct that contains no water and does not have the tendency to absorbwater, is sealed to the penetration of oxygen and for which theproduction process requires only moderate heating. Further, it isadvantageous that non-EFA components of the food product be healthy orat least not harmful.

[0082] All these aims can be achieved by adding EFAs or EFA-rich oils toa product of the present invention. Amongst all other obviousadvantages, it is clear that as the product is virtually water andpreservative free, EFAs in the product remain effective over a longperiod of time.

[0083] The manner in which EFAs are added to any one of the products ofthe present invention is clear. An EFA or EFA containing oil can beadded at any moment to the mixture, ensuring that the EFA is neverexposed to damagingly high temperatures.

[0084] Since the motivation for the addition of an EFA to a viscous oilproduct of the present invention is to make a food with positive healthbenefits, it is clear that it is most advantageous to use the EFAtogether with a healthy oil. Thus, the oil used is preferably olive oil,walnut, macadamia or avocado oil. The most preferred crystallizing agentis lechitin, also having positive health benefits. Akofine PO5® is apreferred crystal stabilizing agent, as Akofine PO5® is nothydrogenated.

[0085] When an EFA-containing oil has an acceptable flavor, theEFA-containing oil may be used directly as an oil in the method of thepresent invention to make a spread. For example EFA-containing borageseed oil can be used as oil for making a surprisingly tastyGLA-containing “borage seed margarine”.

[0086] Preferred EFAs include: DHA and EPA from any source, mostpreferably as components of fish oil; ALA from any source, preferably ofnon-animal origin, most preferably as a component of flax, camelina orsafflower oil; GLA from any source, most preferably as a component ofborage seed or primrose oil; CLA, pure or as mixtures, especially 8-cis,10-trans linolenic acid from any source. It is clear that it may beadvantageous to combine one or more EFAs in a single tasty viscous oilproduct of the present invention.

[0087] When making an EFA-containing product of the present invention,it is preferable the oil or the mixture of the oil with other componentsbe de-aerated. It is also preferable that mixing, cooling andhomogenization steps be performed under a substantially inert (that isdry and oxygen-less) atmosphere.

[0088] As in other embodiments of the present invention, oils-solubleflavorings, with which one skilled in the art is well acquainted, areadded. In the opinion of the inventor, for fish oil preferred flavorsare garlic, basil, oregano or smoky. For ALA and GLA, preferred flavorsare garlic, basil, and oregano.

SPECIFIC SYNTHETIC EXAMPLES First General Method of Solidified OilProduction Example 1

[0089] To 99.5 gram extra virgin olive oil was added 0.5 gram of stearicacid monoglyceride and heated to 80° C. with stirring. The mixture wasallowed to cool to room temperature, making a viscous oil product of thepresent invention.

[0090] Digital light microscopy (DLM) with differential interference(DIC) and crossed-polar optics was used to observe structural changes atthe micrometer scale as a function of temperature. Lamellar liquidcrystal were observed to be present at a temperature of below 60° C., todisappear at a temperature above 60° C. and to re-form when thetemperature was again lowered to below 60° C. In FIG. 1 is areproduction of a DIC image of the viscous oil product at 25° C. takenusing Nomarski Optics (FIG. 1A) and crossed polar image (FIG. 1B).

[0091] The Theological properties of a viscous oil product of thepresent invention (7% stearic monoglyceride in olive oil) were measured,including viscosity as a function of temperature and shear rates,indicating both liquid and solid properties. A clear increase inviscosity was observed. Differential scanning calorimetry (DSC) confirmsthe phase transformation, see FIG. 2.

[0092] A thin-liquid film of the viscous oil product of the presentinvention was spread on a transmission electron microscope grid at 58°C. in a controlled-environment vitrification system, cooled by immersionin liquid nitrogen and studied using a cryogenic temperaturetransmission electron microscope (cryo-TEM). In FIG. 3 are cryo-TEMimages of viscous oil products of the present invention. In FIG. 3A is areproduction of a cryo-TEM image of a first viscous oil product of thepresent invention (0.5% stearic monoglyceride in olive oil). In FIG. 3Bis a reproduction of a cryo-TEM image of a second viscous oil product ofthe present invention (7% stearic monoglyceride in olive oil). In FIG.3, small parallel lines (for example, inside the dashed square) arelamellar liquid crystals.

[0093] In FIG. 4 is shown the result of a small-angle X-ray scattering(SAXS) of a viscous oil product of the present invention (7% stearicmonoglyceride in olive oil). The sharp peak centered at 1.35 nm⁻¹(spacing of 4.6 nm) and the broad peak centered at 2.70 nm⁻¹ (exactlyone-half of the spacing of the sharp peak) is characteristic of alamellar phase made of small domains. The measured spacing of 4.6 nm isin excellent agreement with the cryo-TEM results.

Example 2

[0094] Crystallizing agent (monoglyceride derivative of palmitic acid, 4g) was mixed with extra virgin olive oil (96 g), heated to 68°-70° C.and subsequently cooled to room temperature to produce a viscous oilproduct of the present invention.

Example 3

[0095] Crystallizing agent (monoglyceride derivative of palmitic acid, 5g) was mixed with extra virgin olive oil (95 g), heated to 68°-70° C.and subsequently cooled to room temperature to produce a viscous oilproduct of the present invention.

Example 4

[0096] Crystallizing agent (monoglyceride derivative of palmitic acid, 6g) was mixed with extra virgin olive oil (94 g), heated to 68°-70° C.and subsequently cooled to room temperature to produce a viscous oilproduct of the present invention.

Example 5

[0097] Crystallizing agent (monoglyceride derivative of palmitic acid, 4g) was mixed with distilled avocado oil (96 g), heated to 68°-70° C. andsubsequently cooled to room temperature to produce a viscous oil productof the present invention.

Example 6

[0098] Crystallizing agent (monoglyceride derivative of palmitic acid, 5g) was mixed with distilled avocado oil (95 g), heated to 68°-70° C. andsubsequently cooled to room temperature to produce a viscous oil productof the present invention.

Example 7

[0099] Crystallizing agent (monoglyceride derivative of palmitic acid, 6g) was mixed with distilled avocado oil (94 g), heated to 68°-70° C. andsubsequently cooled to room temperature to produce a viscous oil productof the present invention.

Example 8

[0100] Crystallizing agent (polyglycerol poly ricinoleate, 10 g) ismixed with extra virgin olive oil (100 g), heated to 75° C. andsubsequently cooled to room temperature to produce a viscous oil productof the present invention.

Example 9

[0101] Crystallizing agent (oleic acid monoglyceride, 10 g) is mixedwith soy oil (110 g) and Cessa Powder 60® (3 g), heated to 65° C. andsubsequently cooled to room temperature to produce a viscous oil productof the present invention.

Example 10

[0102] Crystallizing agent (monoglyceride derivative of oleic acid, 10g) is mixed with soy oil (110 g) and Cessa Powder 60® (5 g) and heatedto 65° C. After a clear mixture is achieved, the mixture is allowed tocool to 58° C. when the mixture begins to appear cloudy. The mixture isthen homogenized by shear-homogenization in a mixer at 8000 rpm andallowed to cool to a temperature of 50° C. room temperature to produce aviscous oil product of the present invention.

Example 11

[0103] Crystallizing agent (lechitin, 6 g) is mixed with fish oil (5 g),extra virgin olive oil (88 g) and Akofine PO5® (1 g), heated to 70° C.and subsequently allowed to cool to room temperature to produce aviscous oil product of the present invention.

Example 12

[0104] A mixture of corn oil (60 g) and borage seed oil (40 g) isde-aerated using nitrogen. Crystallizing agent (propylene glycol monostearate, 6 g), Akofine PO5® (2 g) and lemon essence (0.1 g) are added.The mixture is heated to 70° C. and subsequently allowed to cool to roomtemperature to produce a viscous oil product of the present invention.

Example 13

[0105] To pasteurized tahini (100 g, containing 50% oil) is addedcrystallizing agent (sucrose mono stearate, 1.5 g) and thoroughly mixedThe mixture is heated to 70° C. and subsequently allowed to cool to roomtemperature to produce a homogenous oily paste of the present invention.

Example 14

[0106] Sesame seed are washed, peeled, dried and pulverized in a mill toget sesame flour. Sesame flour (100 g, containing 50% oil) is heated to90° C. to allow pasteurization. After 60 minutes, crystallizing agent(sucrose mono stearate, 1.2 g) is added and the resulting pastethoroughly mixed while being allowed to cool to room temperature toproduce a homogenous oily paste of the present invention.

Example 15

[0107] Crushed peanuts (100 g, containing 50% oil) are mixed withcrystallizing agent (2 g triglycerol mono stearate). The mixture isheated to 70° C. and ground until a homogenous paste is attained. Thehomogenous paste of the present invention is allowed to cool to roomtemperature.

Example 16

[0108] To shelled macadamia nuts (100 g, containing 80% oil) are added 3g palmitic acid monoglyceride and 0.1 g Cessa Powder 60®. The mixture isheated to 70° C. and ground until a homogenous paste is attained. Thepaste is allowed to cool to 60° C. The mixture is homogenized byshear-homogenization in a mixer at 8000 rpm and thereafter allowed tocool to room temperature producing a homogenous oily paste of thepresent invention.

[0109] It will be appreciated that the above examples and descriptionsare intended only to serve as examples, and that many other embodimentsare possible within the spirit and the scope of the present invention.In particular, although the primary focus of the writing hereinabove isfor edible food spreads, it is understood that the viscous oils of thepresent invention may find application in many and varied fields ofhuman endeavor.

1. A viscous oil product comprising a. greater than about 90% by weightof oil; and b. a non-monoglyceride crystallizing agent.
 2. A viscous oilproduct comprising a. greater than about 90% by weight of oil; b. amonoglyceride crystallizing agent; and c. a crystal stabilizing agent.3. A viscous oil product comprising a. from about 15% to about 90% oilby weight; and b. a crystallizing agent.
 4. The viscous oil product ofclaim 1, 2 or 3 further comprising from about 15% to about 90% oil byweight.
 5. The viscous oil product of claim 3 comprising from about 20%to about 90% oil by weight.
 6. The viscous oil product of claim 3comprising from about 30% to about 90% oil by weight.
 7. The viscous oilproduct of claim 3 comprising from about 40% to about 90% oil by weight.8. The viscous oil product of claim 1, 2 or 3 wherein said oil is atleast one of the oils chosen from the group consisting of olive oil,avocado oil, fish oil, rapeseed oil, soybean oil, sunflower oil, peanutoil, safflower oil, cottonseed oil, coconut oil, rice bran oil,mustardseed oil, camelina oil, chia oil, flaxseed oil, perilla oil, palmoil, corn oil, sesame seed oil, peanut oil, almond oil, walnut oil, pinenut oil, macadamia nut oil, borage seed oil, primrose oil.
 9. Theviscous oil product of claim 1, 2 or 3 wherein said oil is at least onefrom the group consisting of palm stearin and palm kernel.
 10. Theviscous oil product of claim 1, 2 or 3 wherein a ratio oil:crystallizingagent is between about 9:1 and about 49:1.
 11. The viscous oil productof claim 10 wherein a ratio oil:crystallizing agent is between about12:1 and about 24:1.
 12. The viscous oil product of claim 3 wherein saidcrystallizing agent is a monoglyceride.
 13. The viscous oil product ofclaim 2 or 12 wherein said monoglyceride is selected from the groupconsisting of oleic acid derivatives and palmitic acid derivatives. 14.The viscous oil product of claim 1 or 3 wherein said crystallizing agentat least one of the crystallizing agents chosen from the groupconsisting of lechitins, monoglyceride esters, diglyceride esters,polyglycerol esters of fatty acids, propylene glycol difatty acidesters, sugar esters of fatty acids, sodium stearoyl lactylates,potassium stearoyl lactylates and polyglycerol poly ricinoleate.
 15. Theviscous oil product of claim 14 wherein said crystallizing agent is atleast one of the crystallizing agents chosen from the group consistingof phosphatidyl serine lechitin, phosphatidyl choline lechitin,decaglycerol decastearate (10.G.10.S.), diglycerol monostearate(2.G.1.S.), diglycerol monopalmitate (2.G.1.P.), triglycerolmonostearate (3.G.1.S.), triglycerol monopalmitate (3.G.1.P.),hexaglycerol monostearate (6.G.1.S.), hexaglycerol tristearate(6.G.3.S.), decaglycerol octostearate (10.G.8.S.), decaglyceroloctopalmitate (10.G.8P.), propylene glycol mono stearate (PGMS),propylene glycol stearate (DPGMS), sucrose mono stearate, sucrosemonopalmitate, sucrose monolaurate, sucrose monooleate and polyglycerolpoly ricinoleate (PGPR).
 16. The viscous oil product of claim 1 or 3further comprising a crystal stabilizing agent.
 17. The viscous oilproduct of claim 16 wherein said crystal stabilizing agent is a powderedfat with a melting point less than about 80° C.
 18. The viscous oilproduct of claim 17 wherein said powdered fat is at least one of thecrystal stabilizing agent selected from the group consisting of AkofinePO5®, Akofine R®, Akofine K25®, Akofine SP01®, Akofine D08® and AkofineWOO® and Cessa Powder 60®.
 19. The viscous oil product of claim 2 or 16wherein a weight of said crystal stabilizing agent is between 0.001% and5% of the weight of said oil in the viscous oil product.
 20. The viscousoil product of claim 19 wherein a weight of said crystal stabilizingagent is between 0.1% and 2% of the weight of said oil in the viscousoil product.
 21. The viscous oil product of claim 1, 2 or 3 furthercomprising at least one of the additives from the group consisting ofessential fatty acids, oil-soluble vitamins and oil-soluble flavorings.22. The viscous oil product of claim 21 wherein a said essential fattyacid is chosen from the group consisting of DHA (docosahexaenoic acid),EPA (eicosapentaenoic acid), ALA (alpha linolenic acid), GLA (gammalinolenic acid), CLA (conjugated linolenic acid) and 8-cis. 10-translinolenic acid:
 23. The viscous oil product of claim 21 wherein a saidessential fatty acid is supplied as a component of one of a groupconsisting of fish oil, flax oil, camelina oil, safflower oil, borageseed oil and primrose oil.
 24. A method of producing a viscous oilproduct comprising a. mixing at least one oil and at least onenon-monoglyceride crystallizing agent to make a mixture, said mixturebeing at least about 90% oil; b. heating said mixture; and c. subsequentto said heating, cooling said mixture.
 25. A method of producing aviscous oil product comprising a. mixing at least one oil, at least onemonoglyceride crystallizing agent and a crystal stabilizing agent tomake a mixture, said mixture being at least about 90% oil; b. heatingsaid mixture; and c. subsequent to said heating, cooling said mixture.26. A method of producing a viscous oil paste comprising a. mixing atleast one oil-containing product and at least one non-monoglyceridecrystallizing agent, said mixture being from about 15% to no greaterthan about 90% oil by weight; b. heating said mixture; and c. subsequentto said heating, cooling said mixture.
 27. The method of claim 24, 25 or26 wherein said heating is to a temperature of between about 45° C. andabout 120° C.
 28. The method of claim 24, 25 or 26 wherein said heatingis to a temperature of between about 45° C. and about 90° C.
 29. Themethod of claim 24, 25 or 26 wherein said heating is to a temperature ofbetween about 45° C. and about 75° C.
 30. The method of claim 24, 25 or26 wherein a ratio of said oil to said crystallizing agent is between 9to 1 and about 49 to
 1. 31. The method of claim 30 wherein a ratio ofsaid oil to said crystallizing agent is between 12 to 1 and about 24to
 1. 32. The method of claim 26 wherein said oil-containing product isan oily paste.
 33. The method of claim 24, 25 or 26 wherein said heatingsaid mixture includes pasteurization of said mixture.
 34. The method ofclaim 26 wherein said oil-containing product is a solid.
 35. The methodof claim 34 wherein said oil-containing product is selected from thegroup of grains, chunks, nuts, seeds, fragments, powders, flours anddusts.
 36. The method of claim 34 wherein said mixing includes givingsaid mixture a paste-like consistency.
 37. The method of claim 36wherein said giving said mixture a paste-like consistency includes oneof the actions from the groups consisting of bruising, comminuting,crushing, grinding, mashing, milling and macerating.
 38. The method ofclaim 24, 25 or 26 further comprising reducing size of crystals in saidmixture.
 39. The method of claim 38 wherein said reducing size ofcrystals in said mixture is performed during said cooling.
 40. Themethod of claim 39 wherein said reducing size of crystals in saidmixture is performed by homogenizing said mixture.
 41. The method ofclaim 40 wherein said homogenizing is performed using one of thehomogenizing methods selected from the group consisting of high-shearhomogenization and piston homogenization.
 42. The method of claim 24 or26 further comprising adding a crystal stabilizing agent to saidmixture.
 43. The method of claim 25 or 42 wherein an amount of saidcrystal stabilizing agent added is between about 0.001% about 5% of theweight of said oil.
 44. The method of claim 25 or 42 wherein an amountof said crystal stabilizing agent added is between about 0.1% about 2%of the weight of said oil.
 45. The method of claim 24, 25 or 26 furthercomprising adding an essential fatty acid to said mixture.
 46. Themethod of claim 24, 25 or 26 further comprising de aerating said oil.47. The method of claim 24, 25 or 26 further comprising maintaining saidmixture in an inert atmosphere.
 48. A method of making a viscousoil-containing product comprising: a. providing a non-monoglyceridecrystallizing agent capable of forming lamellar liquid crystals in oils;b. providing an oil-containing substrate; c. dissolving saidcrystallizing agent in said oil-containing substrate at an elevatedtemperature; and d. cooling said mixture so as to allow formation oflamellar liquid crystals.
 49. A method of making a viscousoil-containing product comprising: a. providing a monoglyceridecrystallizing agent capable of forming lamellar liquid crystals in oils;b. providing an oil-containing substrate with an oil content of betweenabout 15% and about 90%; c. dissolving said crystallizing agent in saidoil-containing substrate at an elevated temperature; and d. cooling saidmixture so as to allow formation of lamellar liquid crystals.
 50. Theuse of at least one of the compounds selected from a group consisting oflechitins, monoglyceride esters, diglyceride esters, polyglycerol estersof fatty acids, propylene glycol difatty acid esters, sugar esters offatty acids, sodium stearoyl lactylates, potassium stearoyl lactylatesfor the production of lamellar liquid crystals in oil.
 51. The use of atleast one of the compounds selected from the group consisting oflechitins, monoglyceride esters, diglyceride esters, polyglycerol estersof fatty acids, propylene glycol difatty acid esters, sugar esters offatty acids, sodium stearoyl lactylates, potassium stearoyl lactylatesfor the increasing of viscosity in oils.